Azobisisobutyronitrile → HCID 20343345, compound

HRID 2050048Notes

Reaction equation

HRID 2050048 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[CH:7]=[C:8]([CH3:13])[C:9]([F:12])=[CH:10][CH:11]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[CH:7]=[C:8]([C:9]([F:12])=[CH:10][CH:11]=1)[CH2:13][Br:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 20343346HCID 20343346, compound

Product 1

HCID 20343345HCID 20343345, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
10 °C

Procedure

48.4 g (0.22 mol) of 3-(3-fluorophenoxy)-6-fluorotoluene were dissolved in 300 ml of anhydrous carbon tetrachloride and heated under reflux with 41 g of N-bromosuccinimide. After 70° C. was reached, 3 g of azo-diisobutyronitrile were added; after about 10-20 minutes the reaction commenced, with evolution of heat, and after the exothermic reaction had subsided the mixture was heated under reflux for a further 4 hours. The reaction batch was then cooled to 10° C., the succinimide was filtered off and the carbon tetrachloride was distilled off in vacuo. The oil which remained was distilled at 142°-150° C./2 mm Hg. 3-(3-Fluorophenoxy)-6-fluorobenzyl bromide was obtained in 51% yield.

Workup

  1. temperatureheated
  2. customAfter 70° C.
  3. customafter about 10-20 minutes the reaction commenced
  4. temperaturewith evolution of heat
  5. customafter the exothermic reaction
  6. temperaturewas heated
  7. temperatureunder reflux for a further 4 hours
  8. filtrationthe succinimide was filtered off
  9. distillationthe carbon tetrachloride was distilled off in vacuo
  10. distillationThe oil which remained was distilled at 142°-150° C./2 mm Hg

Sources & evidence

ORD record
ord-38f63836358e4099a5103ff96aad8410
Source dataset
uspto-grants-1980_04
Patent number
US04199596

Reaction notes

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